Pyridine-2-carboxylic acid [2-(4-nitro-phenyl)-3H-imidazo[4,5-c]pyridin-6-yl]-amide → Pyridine-2-carboxylic acid [2-(4-amino-phenyl)-3H-imidazo[4,5-c]pyridin-6-yl]-amide

HRID 854091Notes

Reaction equation

HRID 854091 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[NH:27][C:13]3[CH:14]=[N:15][C:16]([NH:18][C:19]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=4)=[O:20])=[CH:17][C:12]=3[N:11]=2)=[CH:6][CH:5]=1)([O-])=O>C1COCC1.CO.[Ni]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[NH:27][C:13]3[CH:14]=[N:15][C:16]([NH:18][C:19]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=4)=[O:20])=[CH:17][C:12]=3[N:11]=2)=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 58932934Pyridine-2-carboxylic acid [2-(4-nitro-phenyl)-3H-imidazo[4,5-c]pyridin-6-yl]-amide

Product 1

HCID 58932927Pyridine-2-carboxylic acid [2-(4-amino-phenyl)-3H-imidazo[4,5-c]pyridin-6-yl]-amideYield 88.6%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A solution of amide 21 (0.80 g, 0.222 mmol) in THF/MeOH (5 ml/5 ml) was stirred with Raney Nickel (0.150 ml) under H2 atmosphere at room temperature for 2 h. The amine was freed from catalyst by filtration through celite to give 22 (0.065 g, 88%) dried and used as is for the next step.

Workup

  1. filtrationThe amine was freed from catalyst by filtration through celite

Sources & evidence

ORD record
ord-57af4e84655a4373bcd34189cb36a4e3
Source dataset
uspto-grants-2007_08
Patent number
US07256287B2

Reaction notes

Loading…